How Should Cowboy Boots Fit? Fitting Tips for Fashion and Comfort


Planning to pull the trigger on that cowboy look?

Are you currently searching for the next pair that will complete the outfit but are unsure how to fit cowboy boots?

Whether it is your first time buying a pair of cowboy boots or you just want to know what’s wrong with the last five pairs you recently bought, you came to the right place!

Here, you will learn all the necessary details to pick the right pair of cowboy boots. More than just the look and styles, it is an important factor that a cowboy boot fit perfectly so you can walk comfortably.

So, let’s get started looking for the right boots!

How Should Cowboy Boots Fit?


How Should Cowboy Boots Fit
Echo Valley Ranch ( is licensed with CC BY-ND 2.0. To view a copy of this license, visit

Fitting cowboy boots is not the same as with other shoes, like sandals or sneakers. You’ve done the latter so many times in your life; it does’nt take too much thought when buying one of those.

But when it comes to this specific pair of boots, it is a bit trickier. First, they are made with a sturdy and tough exterior, so the common pressing-on-the-toe-box-technique to check for enough space is not feasible. You need to find another way to know if the boot fits.

To do that effectively, you must be familiar with the different parts of a cowboy boot, and later on, we will discuss how each one should fit and feel.

Let’s take a quick look at these cowboy boot parts.


This is the part of the cowboy boot that covers the upper surface of the foot, between the heel/ankle and the midfoot (which is often called the “waist”). It greatly determines if the boot will be a comfortable fit or not.


The boot’s ball is where it usually bends when taking a step. It is located at the widest part of the boot where the ball of your foot is.


The heel of a cowboy boot is more than just for fashion, it’s designed to prevent heel slip. They are located right where your foot’s heel is, thus the name.

Toe Box

This is the part of the boot covering the toes and the front part of the foot. It is often hard, so the toe-press trick will not be helpful but can damage the toe box if too much pressure is exerted.

Now that you are familiar with the parts of these western boots, it’ll be clearer as we go on with the tricks and tips on how cowboy boots fit.

How Does a Perfect Fit Look?


snakeskin cowboy boots
“Cowboy Boots” by Chun’s Pictures is licensed with CC BY 2.0. To view a copy of this license, visit

If you are new to cowboy boots, you must always take into consideration how the instep feels. It must be snug enough to keep the heel in place, but not so tight that blood cannot freely circulate, because that’s exactly what would cause discomfort.

The toes must have enough room to wiggle; just the right amount of space so that they are not cramped together. So instead of the “press-test” to determine the proper fit of the boot, you must do the “wiggle-test” instead to check if the toe is comfortable.

As for the heel, a half-inch or less of heel slippage at the outset should not be a concern. Once you are done breaking them in, this will eventually adjust. It can even be necessary that the initial slip is there to make room for the boot to adjust to your foot as it wears in.


Shopping for cowboy boots
“Shopping for cowboy boots” by Visit Grand Island is licensed with CC BY 2.0. To view a copy of this license, visit


How to Find the Correct Size

Choosing the right cowboy boots size will ensure that they will fit well and comfortably in the long run. Don’t worry: the break-in period doesn’t take too long. Some boots should feel right the moment you get them, like Western-style boots.

It is easy to say that you must get the right size of boots, but it can be quite a challenge without the proper knowledge about this kind of footwear.

Cowboy boots do not have shoelaces, so there is no way for you to adjust the fit. You have to be familiar with the material to know how much allowance you need to consider to break-in new cowboy boots.

Special Considerations In Choosing the Right Size

I don’t want to overwhelm you with too many technicalities about boots, so we will focus on the crucial points you need to note to get the right cowboy boots fit.

My Red Wing Iron Ranger review gives more details on style, length, and how to properly wear boots, and more, check it out!

How It Fits the Calf

A notable aspect of classic cowboy boots is how they are crafted to heights that reach the calf. These leather shoes are made that way for a purpose since, by definition, cowboys use them. They need extra protection from muds and other elements as they work around the farm.

All of us have different calves; some are big, others are small, and it’s not dependent on whether you have narrow feet.

That is why this area should not be your main focus when you fit cowboy boots. The wiggle room could just be a half-inch or two inches. The vital measure is if they are a comfortable fit on the toes and feet, and there are no remarkable foot slides.

For those who want to keep the calf inside their jeans, it would be smart to pick a pair of cowboy boots with narrow width. If you have tried a boot on, and all works fine except the calf, you may want to consider having it altered by professionals to suit your needs.

[Related: How to Stretch Cowboy Boot Calves]

Focus On The Instep

One of the telltale signs that you got the wrong boot size is when the ankle seems to be slipping too much. Earlier, we discussed how the heel works and how we should not be worried when there is a bit of a slide, but that would be an issue if the ankle is too loose.

If this is the case, you have to check the instep. This area must feel snug. It is a crucial aspect for a new pair of boots because, unlike other types, it has no laces which you can adjust to make the leather boots fit. The foot is dependent on the instep to keep it in place as it pushes back to the heel.

Again, the maximum allowable heel slip is around half an inch. This is so that when the material has adjusted, there is enough breathable space for your foot. The heel slippage will eventually be gone once the leather boots softened. Beyond that allowance, it means the boots are too big.

On the other hand, the instep of your cowboy boots may be considered too small if you feel it is too tight that blood circulation feels hindered.

The instep could be a challenge at first when you fit cowboy boots because they do not yield so easily. Initially, you may need blister pads or band aids to protect your heels. We also recommend wearing boot socks. Wear it with socks to keep the feet dry until the break-in is done.

[Related: 5 Tips to Avoid Blisters With New Boots]

Mind the Pull Tab

You will notice that most traditional cowboy boots are made with pull tabs. The pull-tab is that part of the boot that helps make it easier to pull up as you put your feet in. Some varieties of this are mule ears or pull holes.

Pull-tabs are very useful in comfortably trying on your new boots. However, if you require much effort in pulling up the boot, it could mean that what you got is a bit small. These must only be used for support because they could also be ripped off if too much force is applied.

See If The Ball Matches

When checking if the boot you picked is the right one, you can do the initial sizing up by matching the widest part of your foot (the ball of your foot) to the widest part of the boot. If this matches, it is very likely that the boot fits.

Then again, this is just to get started. You still have to try it on and see if the other aspects mentioned above are met. That match must be met because that will determine if you got the flex points right.

Flex points are where your feet tend to bend. It would help that your leather boots fit well on this part of your body, as it can be very uncomfortable and may even cause injury otherwise. Although boot manufacturers of many brands are keen on this, it is still crucial that you know this matter when shopping for a new pair of boots.

Choose the Toe Shape


snake skin cowboy boots
“Now THIS is how you do snake skin cowboy boots” by dpstylesô is licensed with CC BY 2.0. To view a copy of this license, visit

Cowboy boots come in different toe styles and sizes. Choosing a specific boots design will largely depend not just on your fashion taste but also on the length of your toes.

Not all options apply to all types of toes. For example, a square-toed leather boot can make long toes feel cramped. If your toes are spread out, and you have wide feet, getting a pointed-toe leather boot may just create friction on the edges.

When deciding, you must remember this: if it feels uncomfortable when you try to fit cowboy boots in the store, it will not get any better even after breaking in. So, when you feel even the slightest inconvenience on your toes, just get a different one.

Should You Size Up?

When it comes to boots, you don’t usually have to. All you need is to go to the store yourself and start trying them out. Walk with socks on, feel if it is snug, check if it will slip, and follow the boot fit guide.

It is one of the things in life that you cannot just delegate if you want to land on the one that will fit and which you can wear. Trying new boots on is crucial to ensure that you will get the perfect cowboy boots to complete your get-up.

Breaking in your cowboy boots does not take too long. As stated earlier, there are boots that fit the foot so naturally the first time that very minimal adjustments would take place. So, just stick to your normal shoe size and style unless otherwise directed by the manufacturer (for instance, if they advise you to size down).

Boots Up!


Cowboy Boots at SXSW 2010
“Cowboy Boots at SXSW 2010 – South by Southwest” by David Berkowitz is licensed with CC BY 2.0. To view a copy of this license, visit

Now that you know what a nice pair of cowboy boots should fit like, it’s time to get that lasso and feel the vibe!

You know now how to choose the right size and fit for your cowboy boots to make your feet feel comfortable. Just the boot fit guide mentioned above, and you will never go wrong when you fit cowboy boots.

To learn more about lace up boots, check out my Thursday Captain Boot Review!

You should still be quite cautious as human error may always occur. Make sure that you keep the receipt and see if there is a way you can return the item in case you realize later on that you made a mistake.

Most stores would allow a few days for exchanging items. If that is the case, try wearing the boots around your home for some time, either as you walk or sit, to see if you indeed got the right fit, snug and all.

Go ahead and buy those cowboy boots. Let the break-in begin!

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Mel Compo

Mel Compo is a writer, editor, and general word-geek from Brooklyn, New York. When they’re not writing about the finer side of men’s footwear they can be found lurking around the streets, trains, and museums of NYC, ostensibly doing something urgent but actually just looking around for menswear style inspiration.

2 thoughts on “How Should Cowboy Boots Fit? Fitting Tips for Fashion and Comfort”

  1. Cowboy boots is particularly durable. I have been the use of them for the final 10 months, and they may be running high-quality. Anyone seeking out a Cowboy boots trouble would love this. Just my cents. Thanks.


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